Aminoacetaldehyde dimethyl acetal → 2-(3-nitrophenyl)-1H-imidazole

HRID 322064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 322064
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7](=[NH:10])OC)([O-:3])=[O:2].CO[CH:16](OC)[CH2:17][NH2:18]>CO>[N+:1]([C:4]1[CH:5]=[C:6]([C:7]2[NH:18][CH:17]=[CH:16][N:10]=2)[CH:11]=[CH:12][CH:13]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 122008323-nitro-benzimidic acid methyl ester

Produkt 1

HCID 8210012-(3-nitrophenyl)-1H-imidazoleAusbeute 48,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A stirred solution of methyl 3-nitrobenzimidate (7.57 g) and aminoacetaldehyde dimethylacetal (5.57 g) in methanol (20 ml) is heated under reflux for 24 hours. The cool solution is evaporated, and the residue treated with water (9.5 ml) and conc. hydrochloric acid (21 nil). The mixture is heated (steam bath) for 15 minutes and evaporated under reduced pressure. Water (50 ml) is added to the residue and the insoluble solid filtered and washed with water. The filtrate is neutralized with potassium carbonate solution and the precipitated solid filtered and washed with water. The combined solids are charcoaled and recrystallised from ethanol to give 3.87 g of 2-(3nitrophenyl)imidazole, mp 193-194.5° C.

Aufarbeitung

  1. temperatureunder reflux for 24 hours
  2. customThe cool solution is evaporated
  3. additionthe residue treated with water (9.5 ml) and conc. hydrochloric acid (21 nil)
  4. temperatureThe mixture is heated (steam bath) for 15 minutes
  5. customevaporated under reduced pressure
  6. additionWater (50 ml) is added to the residue
  7. filtrationthe insoluble solid filtered
  8. washwashed with water
  9. filtrationthe precipitated solid filtered
  10. washwashed with water
  11. customrecrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-c2438538b363415a82764565feb8661b
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211220B1

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